Last week, I hit an inflection point – a shift in perspective that altered how I see AI, and will shape everything I do going forward.

My history with tech waves

I came of age amidst the rise of the internet and social media.

In middle school I was on AIM chat rooms. (Don’t tell my parents, but I regularly snuck into the “mature” chat rooms when nobody was watching.)

Facebook arrived on my college campus during freshman year. I joined right away, but was hesitant to share my face online.

In 2007, when a college friend showed me his first iPhone, I was skeptical. It didn’t have a keyboard and felt flimsy in my hand.

When I moved to San Francisco in 2008, the world was reeling from the real estate crash. An industry that I’d been told my entire life was stable, bedrock, had dropped precipitously.

When I was training gymnastics at Stanford University in 2012, several of the guys I practiced with were in crypto and tried to encourage me to buy. I’ve since seen three crypto boom and bust cycles.

Pattern recognition

I started Responsive Conference out of my own desire to explore the future of work, and many of these trends.

I’ve met world experts on trends that became commonplace just a few years later – remote and distributed work, diversity & inclusion, blockchain, and more.

We talked about AI on stage back in 2019! But something is different now.

Casual early adoption

I’ve been using AI in my daily work for several years.

Ten years ago in video you had to manually transcribe an interview before editing. Now our transcriptions at Zander Media can be done in seconds.

I ask ChatGPT to review my articles for structure, grammar, and semantics. I nearly always search on ChatGPT instead of Google.

I’ve known AI is important, but not taken it more seriously than I did the rise of blockchain and crypto, social media, or even AOL chatrooms.

My philosophy has been that of a casual early adopter, “Oh, look! The world’s changed again. And I still need to go train my handstands.”

This one is different

Last week, I hit an inflection point, which happened for two reasons.

My girlfriend is a data scientist and through her daily work she already knows that AI is a tectonic shift.

Then, I listened to this conversation with Tyler Cowen, which I highlighted in Snafu last week.

In the interview, Tyler talked about the significance of AI, the differences between the major LLMs, and how he uses each of them. I was struck by how much I didn’t know.

I was chatting with my father over the weekend, and casually mentioned that AI was going to be the next electricity. He said, reservedly, that he might agree. I’ve since come to believe that AI represents the biggest disruption any of us have ever witnessed.

Bigger than the printing press

I believe AI is going to be bigger than social media, the internet, electricity, or the printing press.

A basic premise of Responsive.org is that the rate of change is accelerating. But just like humans aren’t very good at understanding compound interest or logarithmic growth, we aren’t good at comprehending what it means when a growth curve goes nearly straight up.

I’m not an engineer. I don’t understand machine learning, deep learning, or the math behind LLMs. And I’ve never been caught up in a hype cycle before. I wasn’t all-in on social media, even though I was there at the beginning, or crypto, even though I knew people who were.

But as a lifelong lover of books, I’ve always said that I wished I was there for the advent of the printing press. This is that moment.

My commitment

In a world that is on the verge of disaster – climate, socio-political unrest, and more – AI has the potential to be the collaborator we need to solve these issues. Equally, these tools have the potential to manipulate and destroy us.

My new commitment is to use these tools every day. In my current research of real estate, I’ve 10x my rate of learning by treating ChatGPT as a thought partner. While everything I write in Snafu will continue to be my own, I’m using these tools to hone my craft.

At Responsive Conference, people have been talking about AI on stage since 2019. But in 2025 I want to give attendees a direct taste of these tools as part of the conference experience.

We’re at the beginning of a new era. One that has the potential to be both awe-inspiring and terrifying. We’re not just building new tools – we’re building something smarter than ourselves.

How do we want to participate? How do we reinvent ourselves even faster than the tools that are learning from us? That remains for all of us to decide.

Three weeks ago, my girlfriend and I were looking at rentals just south of San Francisco. Over the course of a long afternoon, we looked at seven different properties.

The next evening, she messaged me a new Zillow listing – this time for a property for sale.

I walked over and wrote her a note: “Fuck it, let’s buy!”

What followed were weeks of going deep down a new rabbit hole. I spoke to hundreds of people, interviewed friends and family about real estate, and we put in four offers on a house.

The world is too loud

In a world rife with distraction, falling down a new rabbit hole isn’t always escapism. Sometimes it’s how we survive.

The allure of breaking news, the infinite scroll of a social feed… Amidst the chaos of modern life, the ability to go deep – to immerse yourself completely in something new – isn’t just useful. It can be a source of sanity.

The sanity of obsession

When the world is chaotic, most of us turn to distraction – even when those distractions leave us feeling worse.

Early in the COVID-19 pandemic, I watched some of the Netflix Documentary Tiger King. While it was a welcome distraction, I came away feeling buzzed and empty.

By contrast, a true rabbit hole – one with structure, challenge, and stakes – isn’t escapism.

My world view changed when I walked into a gymnastics gym at 17 years old and began to learn gymnastics. That rabbit hole has consumed me ever since. Similarly, when I studied ballet obsessively for a year, founded Responsive Conference to study the future of work, or started Zander Media to practice storytelling.

Deep learning is a way to regain control over your attention and expand your world view.

Learning is often conflated with speed, with getting more done in less time. I have studied speed reading, memory palace memorization, and other learning “hacks,” but what interests me more is depth, breadth, and languor.

But my goal with real estate wasn’t just speed. It was depth. Amidst the chaos of the world, it was restorative to spend a few hundred hours researching with ChatGPT, calling dozens of realtors and brokers, interviewing friends, and immersing myself in a new discipline.

Finding your rabbit hole…

Here are three questions I’ve been finding it useful to consider when embarking on a new learning journey.

Why this?

My girlfriend and I were ready to buy our first home. There was a specific house that we were interested in. And, as a friend said to us, “You have to live somewhere.”

Why are you studying this domain right now? That will guide your rabbit hole learning journey.

Why now?

With real estate, we had a very clear rationale.

There were several options available to us – including renting for a year, a short term rental, or finding a house very near term that we wanted to buy.

Why are you interested in doing this journey, and why now?

What’s your deadline?

I’m a proponent of external deadlines. Without deadlines, I will put off until next month something that I could equally accomplish this afternoon.

But when I have a deadline – a person I’m accountable to, a place that I want to live – I’m capable of more than I’d previously have thought possible.

Why rabbit holes matter

The world is chaotic. There’s more distraction and noise on the front page of any news outlet or social media platform than any of us should be consuming.

Deep learning forces us to focus on depth – on something that actually matters. And in a world that’s only getting noisier, that kind of focus is how we stay sane.

I was at dinner with my parents and my girlfriend last weekend. For some reason, Robin’s Cafe came up in conversation.

Anyway, I got on my soap box and said: “I opened Robin’s Cafe on 3 weeks notice and…” Before I could finish the sentence, my father said “And you sold it on Craigslist. We know! We’ve all heard that story many times before.”

My girlfriend, who has recently been subjected to me repeating the story on Zoom calls many times a day, doubled over laughing.

I’m proud of having started and sold Robin’s Cafe. But that also happened nine and five years ago, respectively. I’ve lived through several life changing experiences since then. Relationships and breakups, a car crash, the death of a family member, my best friend’s cancer, and a couple new businesses.

But because Robin’s Cafe was a formative experience – and doubtless because I’ve told the story a few too many times – that narrative has become part of my identity.

We don’t talk enough about identity

Identity isn’t fixed. It is malleable. Our “residual self-image,” to quote The Matrix, should change and adapt over time.

When big life experiences happen, those moments shape us. As they should! But it is up to us to decide for how long and to what extent we want to refer to them forever after.

When she laughed

When my girlfriend burst out laughing (and, to be fair, we’ve both been laughing about that moment ever since), I was forced to reconsider the story and the identity I’ve tied to it.

I’ve reiterated it so many times now that it’s become ossified. And instead of tackling something new, I’m referencing something that took place nearly a decade ago.

Because my girlfriend loves me, her laughter allowed me to laugh at myself. At the ridiculousness of continuing to reference something that, in my life, might as well be ancient history. Her laughter allowed me to see myself through a new perspective and shake up a longstanding identity – that of the person who did those things.

Hold fewer identities

One of my goals in life is to remain resilient. And one of the best ways to maintain resilience is to hold fewer identities, and hold them loosely.

We all know a former high school athlete who recalls their peak performance on the high school football team instead of going to gym today. Or the political stickler who can’t see a perspective other than their own.

I’m an athlete, a son, a partner, a dog dad, and an entrepreneur. And, apparently, I used to be a coffee shop owner.

Moving beyond Robin’s Cafe

Of course, I’ll reference Robin’s Cafe again. I’ll probably even tell the story of opening and selling it to someone new. But my Dad’s joke, which landed so poignantly because of my girlfriend’s good humor, highlighted that I still hold that specific identity too firmly.

It’s time to let it go, so that I can go and do something new.

In 2015, the authors of Responsive Org wrote that “the future is becoming increasingly difficult to predict.”

Today, with global instability, political partisanship, and an ever more rapid rate of change, those words seem prescient.

The tension between organizations optimized for predictability and the unpredictable world we inhabit has reached a breaking point. Only organizations built to adapt are going to survive.

I founded Responsive Conference because I had witnessed the same organizational dysfunctions and habits across nearly two dozen different industries.

In selling to the Fortune 100s, I learned how much of business is relationship-driven. As the first employee at a non-profit education tech company, I witnessed how slow our educational systems are to change. As an acrobat with the San Francisco Opera, I experienced the century-old practices of one of our most storied arts institutions. And in my own little brick-and-mortar restaurant, I learned about San Francisco city politics.

We still structure our organizations for a time where predictability mattered more than speed.

The theme of Responsive Conference 2025 is “Design for change” because the world is changing so rapidly. Only those individuals and organizations that keep pace with change are going to survive.

I hope you’ll join us at the Oakland Museum of California for Responsive Conference 2025.

Let’s build the future of work together!

Get your tickets now!
Prices go up March 15

I love the phrase “mise-en-place,” which is common to professional kitchens and translates to “everything in its place”. The phrase appeals to my inner neat freak.

In restaurants, chefs arrive hours prior to service starting to prepare for the evening ahead. These are the unseen and unsung aspects that make a restaurant successful.

We had a Zander Media video shoot at our film studio in Berkeley last week, and had a luxurious four hours to set up before the clients arrived on set! As a result, it was among the best lit shoots we’ve ever done.

Mis-en-place in a restaurant means arriving hours ahead of time to prepare your ingredients and workspace. Mis-en-place in my video business means keeping our gear closet clean, our batteries charged, and knowing what we need to film long before the actual day.

Preparation matters, but it is only as part of the equation.

Change is coming

In November 2022, OpenAI launched ChatGPT. At the company’s internal meeting that morning, they discussed that it would be a silent launch, and that “no significant impact on sales” was expected, since the “audience is mostly researchers.”

They couldn’t have been more wrong.

In the thirty months since, we’ve seen a complete transformation of the technology industry. There have been macroeconomic swings – seesawing markets and mass layoffs. The biggest tech companies are pouring billions of dollars into AI, while also laying off thousands of workers.

AI has changed how we work. But the emergence of AI drives home the broader lesson that any organization or industry can be shaken up at any moment.

Operating amidst chaos

The premise of Responsive.org is that the world is changing more rapidly than we have ever seen before in human history. This wasn’t an accepted fact when the manifesto was written a decade ago. But today, especially because of the acceleration brought on by the COVID-19 pandemic, we take this acceleration for granted.

The lifespan of the most successful companies in the world has plummeted over the last three decades. Companies on the S&P 500 are expected to remain in the index for an average of fifteen years, compared to sixty-one years in 1958. The only companies that survive are those that adapt quickly to change.

The world we are living in is chaotic. It is no longer the case that the unexpected might happen. It can, and probably will, happen at any moment.

Mise-en-place is important. Preparation does matter. But at least as important is the ability to regulate your own response.

The Serenity Well habit

When my good friend was preparing for the birth of his first child, I asked him what he was doing to prepare. He said that while his wife was reading all of the baby books she could find, he was “digging his serenity well deeper.”

Financial stability, strong relationships, and physical health all matter. But none of them directly solves your uncertainty and stress.

What I call the Serenity Well habit – cultivating internal well-being and calm – is your best buttress against chaos. Here are three practices that can help:

Daily discomfort – Train yourself to handle chaos by introducing small stressors, or eustress. Cold exposure, fasting, intense workouts, public speaking — lean into discomfort.

Reset rituals – Build a system that keeps you grounded. This could be meditation, journaling, a morning routine, or a hot bath before bed.

Contingency planning – How do you want to respond when you’re overwhelmed? Decide in advance how you want to handle stress: a breathing exercise, a workout, stepping away.

The world isn’t going to get calmer. It is time to start digging your serenity well.

SNAFU is an acronym for Situation Normal: All Fucked Up. The phrase was born out of the chaos of World War II, but it is just as relevant today.

Snafu has become my shorthand for a world that’s always been broken, but is now undeniably so. Things that once seemed stable – governments, economies, industries – are changing too quickly for us to keep pace. Technology is advancing faster than any of us can adapt, which reshapes our job, relationships, and culture before we can adapt.

Rules my grandfather espoused – work hard, get a good education, keep your head down and things will work out okay – aren’t just outdated. They’re actively wrong.

For the last decade, I’ve curated a conference about the “future of work”. The premise is that the speed of change is accelerating. That while work in the 20th century was about the illusion of stability, in the 21st century we are watching that illusion disappear.

Political and social unrest are on the rise. Economies are volatile. Climate change and AI have added new layers to that unpredictability. We’re living in an era where the old rules don’t apply, new rules haven’t been written yet, and chaos is the default setting.

Resilience is the only safety net left

When things start to break down, most people – and most companies – look for stability. We all want something or someone to tell us that things will be okay. Stable jobs, trusted institutions, and a plan we can rely on.

Unfortunately, those are an illusion.

The people and organizations who will thrive aren’t the ones who cling to a false sense of stability. They adapt. Resilience isn’t about toughness, but about flexibility. It’s the ability to absorb shocks and keep moving forward.

Resilience is the only real safety net left because we can’t rely on institutions, stable career paths, or a predictable future. We can thrive only by learning to pivot, adapt, and get back up when we fall down.

The key to resilience is learning how to learn

For most of human history, learning specific skills was enough to survive or build a career. We became blacksmiths, factory workers, software engineers, and then did that work for the next few decades.

That’s not how the world works anymore.

The shelf life of knowledge is short. Industries are being reshaped in weeks, not in decades. What you know today may be obsolete tomorrow.

The skill that matters most isn’t what you know—it’s how quickly you can acquire skills and apply that knowledge. How quickly you can change your mind. The skill we most need to survive and get ahead in the world today is meta-learning, or learning how to learn.

Success is about mastering the process of skill acquisition itself. If resilience is the goal, then meta-learning is the most effective way to achieve it.

How I’m surviving the next four years

I have no idea what’s going to happen in the next four years. Nobody does. But things are going to slow down. Here’s how I’m preparing for the next four years.

Physical resilience: Our bodies are the first thing that break down under stress. When I was in a car crash a few years ago, my visible bruises healed in a week, but it took my body nine months to really recover. The way I train for physical resilience is doing little things, every day, that are physically difficult.

I move every day, train to increase strength and endurance, and spend a couple minutes more in a 200 degree sauna than is easy. I’m not chasing peak fitness. I’m chasing a body that can handle stress.

Emotional resilience: Life is unpredictable. Just in the last month, one friend had a mental breakdown and another died. Grief, uncertainty, and failure are inevitable. We can’t control them. But we can train how we respond. I practice emotional resilience by cultivating tiny habits that increase mental fortitude.

One of the best tools I know for emotional resilience is, amusingly, the physical challenge of cold plunging. Through cold exposure, I’m better able to handle the stresses of other, less intense, circumstances. Just getting into the cold plunge (or turning the shower tap to cold) is a victory. Do more things that scare you.

Mental resilience: The key to mental resilience is brain plasticity and avoiding fixed ways of thinking. Do this by limiting your intake of harmful content and by practicing new skills.

The world is full of outrage porn. The business model of the news and social media is to keep you coming back for more. You don’t have to detach from the world in order to limit the amount of content – especially outrageous or toxic content – you imbibe.

Additionally, practice things that stretch you, mentally. I like to sing. I recently started practicing the piano. I’m attempting to learn Darija (Moroccan Arabic). In short, never stop learning.

The world is not going to slow down. The chaos isn’t going away. If anything, things are only going to get more unpredictable!

The only real strategy left is to become the kind of person who can navigate uncertainty with intelligence, speed, and a sense of humor about the absurdity of it all.

Snafu is about that process—learning fast, adapting faster, and finding resilience in a world that refuses to make sense.

A friend of mine just got an 8-week puppy! I’ve raised two dogs from puppyhood, and helped a dozen other people do the same. Here’s what I’ve learned…

Expect interrupted sleep

Interrupted sleep comes with the territory. I often suggest raising a puppy to people who are considering having a child. It’s good practice.

As with a human baby, a puppy needs whatever it needs right now! Whether that’s to be let out in the middle of the night to pee or just your comfort and attention because your puppy has never slept apart from its litter, expect weeks or months of interrupted sleep.

Torn slippers are your fault

Your puppy peeing in the house or tearing up a slipper is your fault.

A young dog doesn’t know, at first, that the house isn’t somewhere to pee. Similarly, an anxious or a teething dog wants to chew. It is up to you to give it something to chew on.

Like a young human baby, a puppy doesn’t have bladder control. It is important to remember that your puppy isn’t doing something wrong. It is just following its natural proclivities.

It is your job to monitor your puppy, so don’t get angry when your dog makes “mistakes.”

Crate training

If I could teach every new dog owner one skill it would be crate training. The first rule of crate training is never use the crate as punishment. Encourage your dog into the crate. Make it cozy. Make it home.

Think of the crate as the spot the dog returns to when it is tired, wants to rest, wants to be alone. A crate has the additional benefit of being a closed container, so your puppy can’t escape and peer and chew your slippers immediately upon waking.

Training cadence

To raise a young dog, develop a training cadence:

• When your puppy first wakes up, take them out of the crate and outside to potty.
• Offer your puppy some water and food.
• Play with your puppy until it is tired.
• Take your dog outside to potty again.
• Put it back in the crate for a nap.

This will be your cadence for the first few months!

Positive reinforcement

Those metal spiked collars people sometimes use are cruel and hurt. A lot of early animal behavior management was done with dolphins. You can’t force a dolphin to do something it doesn’t want to do. The same is true for puppies (and, I believe, humans).

Train your dog exclusively through positive reinforcement.

Negative reinforcement

For minor issues like peeing on the carpet: your puppy didn’t do it to upset you. Even if you catch it in the act, aggressive scolding is more likely to scare your dog than inform it. Puppies don’t yet know how to control their bladder. Focus on reinforcing the behaviors you do want, and the others will fade naturally.

Reinforcement words

In the 1960s, dolphin trainer Karen Pryor used a clicker to train dolphins at Sea Life Park, Hawaii. This marks behaviors before giving a reward. A reinforcement word works the same way.

Pryor popularized clicker training in her book Don’t Shoot the Dog!, a foundational text in positive reinforcement training.

Pro tip: Don’t use “yes”

Pick a word you don’t use daily to mark desired behavior. Otherwise, your dog may get confused.

Your dog reflects your nervous system

When I’m stressed, my border collie Riley is anxious. When I’m calm, Riley is likely asleep. Dogs are mirrors of their owners’ emotional state. Being aware of your own emotions improves your training.

Know their motivation

Some dogs are food-motivated, some aren’t. Some want petting, others want a job. Understand your dog’s motivation first.

Know your breed’s tendencies

• Labradors want attention, praise, and food.
• Herding dogs need a job.
• Bully breeds want to keep their people safe.

Food is a simple, concrete motivator; praise works too but is less tangible. Plan according to breed tendencies.

Say “Come” only when sure

Don’t misuse “Come.” Only call your dog when you know it will obey. Otherwise, you teach them they can ignore you.

Puppies are rude

Puppies lack the social graces of adult dogs. They want attention, to play, to greet, and frolic. Adult dogs may set boundaries; puppies learn social rules through interactions.

You’re the one who needs to change

We have a belief that dog training is about changing the behavior of your dog. Actually, it’s the opposite. Dog training is an opportunity to get to know yourself, and for you to change so that you can become a good steward of your animal.

Your dog is just being itself. If your puppy pees on the floor, it is because you didn’t take it outside in time. If it chews a shoe, you should have given it more opportunity to chew appropriate toys and shouldn’t have left your dog unattended.

Your dog behaves according to its instincts. You are the one who needs to adopt, and only by doing so will you be able to train your dog.

I love when the English language has a word for something that I’m trying to describe that isn’t in the popular vernacular. Today’s word is “eustress,” which means beneficial stress. This kind of experience that is difficult but ultimately does you good.

Eustress is the opposite of distress, which is harmful. It motivates and enhances performance.

How can we build resilience and personal sovereignty in a world that is more chaotic and unpredictable than any time in the last few hundred years? Eustress may be part of the answer.

On the shortness of life

I’m reading the Clan of the Cave Bear series, which is the fictionalized telling of a prehistoric hunter-gathering Cro Magnon society during the last ice age. Throughout these books, life is fleeting and impermanent. At any moment a main character might be killed by a predator, trapped in a blizzard and frozen, or swept downstream in a flood and drowned.

Life is fleeting, but in our modern world we’ve gotten comfortable. I can order food to my door in minutes and travel to the furthest regions of the Earth in days. In our abundant, anything-you-want-at-the-click-of-a-button world, we’ve forgotten how fragile we are.

What doesn’t kill you…

We say that “What doesn’t kill you makes you stronger.” That’s wrong.

I’ve always been good at listening and asking questions, but not carrying the weight of other people’s challenges. Perhaps as a result, I’ve listened to personal anecdotes of some of the most horrific personal acts of violence and violation that a single human can inflict on another. That kind of horror isn’t just stressful; it leaves the victims distressed, traumatized.

What doesn’t kill you doesn’t make you stronger. It leaves most people weaker. There’s survivorship bias; we hear stories of people who come out of difficult situations stronger. Most people who undergo intense trauma end up homeless, depressed, or mentally ill.

Complicating the issue, the right amount of stress for one person will kill someone else. I can do a backflip, but most people attempting a backflip for the first time will land on their head! How much stress is the right amount is specific to each individual, and what’s most beneficial for them.

The only thing each person can do is attempt to add some amount of difficulty – eustress – to their daily lives by evaluating what you are capable of today and then doing something slightly more difficult tomorrow.

Tactics to try

I run 6 miles several days a week. If you ordinarily don’t get outside, perhaps you might go for a walk.

I try to get into my cold plunge for 3 minutes every day. (I don’t make it as often as not.) Maybe your equivalent is a moment of cold water at the end of a hot shower.

Eustress is whatever amount of stress is beneficial for you today. It isn’t the amount of stress useful to somebody else, but the amount you can handle and get stronger through the experience.

The next question is how to get started. Here are two great books about behavior change to get you started:

• The mega-bestseller Atomic Habits by James Clear provides a framework for changing behavior and adopting new habits. James advocates for changing your environment to make change easier.
• The New York Times bestseller Tiny Habits by my old professor BJ Fogg, PhD is a gem. Among other overlooked aspects of the book, BJ teaches deliberate celebration as a mechanism for reinforcing behaviors.

The practice of resilience

Our world today is stressful. Between global conflicts, wildfires, political unrest and global climate change, societies are more rife, challenged, and problematic than most of us have ever seen.

The way forward is through preparing against the worst, while still hoping for the best. The way forward is to practice difficult things before you need to.